866 Pendleton Point Road, Islesboro, ME 04848

New Listing

$5,750,000

Virtual Tour

https://my.matterport.com/show/?m=8TwsGzHEy7x

Property Type: Residential Bedrooms: 6 Baths: 9 Square Footage: 9,449 Lot Size (sq. ft.): 228,690 Status: Active

Current Price: $5,750,000 List Date: 6/16/2026 Last Modified: 6/17/2026

Overview

Description

East Bay is an exceptional coastal estate offering the perfect blend of a private summer retreat and a tranquil year-round residence. Set on more than five secluded acres with 430 feet of pristine, accessible waterfront, the property enjoys an elevated position above the scenic shoreline, where beautifully curated gardens and mature landscaping frame sweeping views across Penobscot Bay and its islands. The residence unfolds along a gently sloping bluff, capturing spectacular water vistas from nearly every room and outdoor living space. Originally built as a post-and-beam home around 2000, East Bay has been thoughtfully transformed over time. Its current design, inspired by the timeless coastal architecture of Royal Barry Wills, combines classic New England character with understated sophistication. Designed for both elegant entertaining and comfortable everyday living, the home offers a seamless balance of formal and informal spaces. Highlights include a first-floor primary suite ... (Read more)

Listing Details MLS# 1667521

Property Sub-Type

Property Sub-Type: Single Family Residence

Location Information

Street #: 866
Street Name: Pendleton Point
Street Type: Road
County: Waldo
Town: Islesboro
State/Province: ME
Zip Code: 04848
Zip +4: 5159
Leased Land: No
Book: 4820
Page: 172
Map: 6
Lot: 6
Zoning: Shoreland Res
Zoning Overlay: Unknown
Association: No
Full Tax Amount $: 47732
Tax Year: 2025
Tree Growth Y/N: No

Contract Information

Original List Price: 5750000

Property Information

Surveyed: Unknown
Seasonal: No
# Rooms: 19
# Bedrooms: 6
# Fireplaces: 4
Total Full Baths: 6
Total Half Baths: 3
Total Baths: 9
Year Built: 2000
SqFt Finished Above Grade: 8696
SqFt Finished Below Grade: 753
SqFt Finished Total: 9449
SqFt Source: Other
Other Source of Square Footage: Matterport Floor Plans, Estimated
Garage: No
Lot Size Acres +/-: 5.25
Source of Acreage: Public Records
Road Frontage: No
Garage Spaces: 0

Water Info

Water Frontage: Yes
Waterfront Amount: 429
Water Frontage Owned: 429
Water View: Yes
Water Body Name: Penobscot Bay, Ocean
Water Frontage Shared: 0

Appliances Included

Other Appliances: See listing remarks
Dishwasher: Yes
Dryer: Yes
Electric Range: Yes
Gas Range: Yes
Microwave: Yes
Refrigerator: Yes
Wall Oven: Yes
Washer: Yes
Other: Yes

More Information

Vehicle Storage

Attached: Yes
1 Car: Yes
Carport: Yes

Site

Level: Yes
Open: Yes
Other Site: Yes
Rolling/Sloping: Yes
Well Landscaped: Yes

Location

Near Country Club: Yes
Near Golf Course: Yes
Near Public Beach: Yes
Other Location: Yes

Roads

Public: Yes

Source of Water Frontage

Public Records: Yes

Water Body Type

Bay: Yes
Ocean: Yes

Construction

Wood Frame: Yes

Basement

Crawl Space: Yes
Finished: Yes
Full: Yes
Partial: Yes
Unfinished: Yes

View

Scenic: Yes

Foundation Materials

Poured Concrete: Yes

Exterior

Wood Siding: Yes

Roof

Shingle: Yes

Heat System

Forced Air: Yes
Heat Pump: Yes
Hot Water: Yes
Zoned: Yes

Heat Fuel

Oil: Yes
Propane: Yes

Cooling

Heat Pump: Yes

Floors

Carpet: Yes
Tile: Yes
Wood: Yes

Parking

5 - 10 Spaces: Yes

Style

Shingle: Yes

Electric

Circuit Breakers: Yes

Gas

Bottled: Yes

Sewer

Private Sewer: Yes

Bedroom 2

Bedroom 2: Yes
Bedroom 2 Level: Second

Water

Private: Yes
Well: Yes

Bedroom Amenities 2

Closet: Yes
Full Bath: Yes

Bedroom 3

Bedroom 3: Yes
Bedroom 3 Level: Second

Bedroom Amenities 3

Closet: Yes
Full Bath: Yes

Bedroom 4

Bedroom 4: Yes
Bedroom 4 Level: Second

Bedroom Amenities 4

Closet: Yes
Full Bath: Yes

Bedroom 5

Bedroom 5: Yes
Bedroom 5 Level: Second

Bedroom Amenities 5

Closet: Yes
Full Bath: Yes

Bedroom 6

Bedroom 6: Yes
Bedroom 6 Level: Second

Bedroom Amenities 6

Closet: Yes
Full Bath: Yes

Driveway

Gravel: Yes

Basement Entry

Bulkhead: Yes
Interior: Yes

Water Heater

Off Heating System: Yes

Amenities

1st Floor Primary Bedroom w/Bath: Yes
Bathtub: Yes
Irrigation System: Yes
Laundry - 1st Floor: Yes
Laundry - 2nd Floor: Yes
Other: Yes
Pool-In Ground: Yes
Primary Bedroom w/Bath: Yes
Shower: Yes
Storage: Yes
Walk-in Closets: Yes

Equipment

Generator: Yes
Internet Access Available: Yes

Dining Room

Dining Room: Yes
Dining Room Level: First

Dining Room Amenities

Wood Burning Fireplace: Yes

Exercise Room

Exercise Room: Yes
Exercise Room Level: Basement

Great Room

Great Room: Yes
Great Room Level: Second

Great Room Amenities

Vaulted Ceiling: Yes
Wood Burning Fireplace: Yes

Kitchen

Kitchen: Yes
Kitchen Level: First

Kitchen Amenities

Eat-in Kitchen: Yes

Laundry Room

Laundry: Yes
Laundry Room Level: First

Library

Library: Yes
Library Level: First

Library Amenities

Wood Burning Fireplace: Yes

Living Room

Living Room: Yes
Living Room Level: First

Living Room Amenities

Built-Ins: Yes
Vaulted Ceiling: Yes
Wood Burning Fireplace: Yes

Primary Bedroom

Primary Bedroom: Yes
Primary Bedroom Level: First

Primary Bedroom Amenities

Closet: Yes
Double Vanities: Yes
Full Bath: Yes
Separate Shower: Yes
Soaking Tub: Yes
Suite: Yes
Sunken/Raised: Yes
Walk-in Closet: Yes

Office

Office: Yes
Office Level: First

Office Amenities

Heat Stove Hookup: Yes

Other Room 1

Other Room 1: Yes
Other Room 1 Level: First

Other Room 2

Other Room 2: Yes
Other Room 2 Level: Basement

Other Room 3

Other Room 3: Yes
Other Room 3 Level: Basement

Room Features

Built-Ins: Yes
Closet: Yes
Double Vanity: Yes
Eat-in Kitchen: Yes
Full Bath: Yes
Heat Stove Hookup: Yes
Separate Shower: Yes
Soaking Tub: Yes
Storage: Yes
Suite: Yes
Sunken/Raised: Yes
Vaulted Ceiling(s): Yes
Walk-In Closet(s): Yes
Wood Burning Fireplace: Yes

Property Features

Site: Level; Open; Other Site; Rolling/Sloping; Well Landscaped Location: Near Country Club; Near Golf Course; Near Public Beach; Other Location Roads: Public Source of Water Frontage: Public Records Water Body Type: Bay; Ocean View: Scenic Appliances Included: Dishwasher; Dryer; Electric Range; Gas Range; Microwave; Refrigerator; Wall Oven; Washer; Other Style: Shingle Construction: Wood Frame Basement: Crawl Space; Finished; Full; Partial; Unfinished Basement Entry: Bulkhead; Interior Foundation Materials: Poured Concrete Roof: Shingle Exterior: Wood Siding Heat System: Forced Air; Heat Pump; Hot Water; Zoned Heat Fuel: Oil; Propane Water Heater: Off Heating System Cooling: Heat Pump Floors: Carpet; Tile; Wood Amenities: 1st Floor Primary Bedroom w/Bath; Bathtub; Irrigation System; Laundry - 1st Floor; Laundry - 2nd Floor; Other; Pool-In Ground; Primary Bedroom w/Bath; Shower; Storage; Walk-in Closets Equipment: Generator; Internet Access Available Driveway: Gravel Parking: 5 - 10 Spaces Vehicle Storage: 1 Car; Carport Electric: Circuit Breakers Gas: Bottled Sewer: Private Sewer Water: Private; Well

Room Information

Room Name	Level
Primary Bedroom	First
Bedroom 2	Second
Bedroom 3	Second
Bedroom 4	Second
Bedroom 5	Second
Bedroom 6	Second
Other Room	First
Library	First
Living Room	First
Dining Room	First
Kitchen	First
Office	First
Great Room	Second
Office	Second
Laundry	First
Office	First
Exercise Room	Basement
Other Room 3	Basement
Other Room 2	Basement

Documents

MLS Packet ›

IDX

Listing Office: Legacy Properties Sotheby's International Realty

Last Updated: June - 17 - 2026

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